Towards Electron Transfer Compounds with Rigid Resistor Units

There is a growing need to access small rigid scaffolds for use in organic and medicinal chemistry. It is a requirement of many systems that the substituents are arranged in a precisely known, specific and invariable orientation. The applications of such scaffold span from host–guest interactions, photosynthesis, light harvesting and energy transfer amongst others. Both triptycene and cubane are rigid three dimensional scaffolds which are capable of arranging substituents in such a spatially defined manner. As a result they are ideal candidates for the synthesis of multiporphyrin arrays, to be used as photosynthetic mimics. In this work transition metal catalyzed cross coupling methodologies such as Suzuki, Sonogashira and Stille reactions have been implemented to successfully attach porphyrins to these hydrocarbon scaffolds.